


Probably Maybe

by tammydiscospider



Category: Community (TV), Definitely Maybe (2008)
Genre: Alternate Universe, Alternate Universe - How I Met Your Mother Fusion, Angst, F/M, Fluff, Romance
Language: English
Status: In-Progress
Published: 2021-03-15
Updated: 2021-03-20
Packaged: 2021-03-23 14:40:42
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 2,625
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/30057018
Author URL: https://archiveofourown.org/users/tammydiscospider/pseuds/tammydiscospider
Summary: As Jeff Winger deals with his looming divorce, his daughter asks him about his love life before getting married.Definitely Maybe AU.Will add characters and tags as the story goes along.
Relationships: Annie Edison & Jeff Winger, Annie Edison/Jeff Winger
Comments: 5
Kudos: 25





	1. Parent Of The Year

Jeff Winger takes a deep breath and stares stares at the piece of paper in front of him. He’s been expecting it, so he’s not really shocked. Still, it’s not a very nice feeling to get your divorce papers. At work. The fact that he’s a lawyer just adds to the irony. He doesn’t move. Why is this so hard, when even he wants this divorce and thinks it’s for the best?

After what feels like an eternity, he takes a look at the wall clock. 3 p.m. on the dot. He breathes a sigh of relief. He stands up, gets his bag and heads out the door, leaving the papers on his desk.

He walks down the streets of New York City, grinning from ear to ear. A smile his nearest and dearest clients do not get to see. Maybe not even his now almost ex-wife. It’s his turn to pick up his daughter from school today. He does it twice weekly and usually leaves the office early. As pumped as he is already, he decides to listen to some music. He takes out some wireless buds and shuffles through his playlist. No, not the one Barenaked Ladies song he secretly likes. He used to be a huge ABBA fan but somehow grew out of it so that’s a no. He finally sees and picks the song “Ants Marching” by Dave Matthews Band (or as he calls them, just Dave). Unfortunately, he accidentally presses the song right before it, “Kiss From A Rose” by Seal. Eh, whatever. It’s a great song and Jeff listens to it anyway. Great way to set the mood. 

He finally reaches the school. It wasn’t that long a walk. Controlling the urge to sing along to his playlist was much harder. As soon as the doors swing open and he enters, he sees absolute chaos.

A sea of people, parents and children fill the halls. Papers flying and screams can be heard all over. It’s a commotion over something but he doesn’t know what. It’s worse than anything he’s seen and he’s worked as a legal consultant for political campaigns.

Thankfully, he sees one of his co-parents, Shirley Bennet, come over to him. She’s just a few years older than him, a single mom and a very devout and religious Christian. He hasn’t told her he’s agnostic since it would disappoint her and he actually finds her very endearing.

“Jeffrey, you will not believe what the Dean has done.”, she says to him. She does not look happy.

“What happened? Is everyone okay? ”, he asks, feeling more concerned now.

“They had a sex education class today.” From her tone, you’d have thought someone was kidnapped.

He lets out a small laugh.

“Sex ed classes? For 10 year olds? That...that is something.” he says, nowhere near as offended as her.

“Laugh all you want now Winger, but just know she’ll be asking you all about it.”

This is enough to wipe the smirk off his face. That had not occurred to him. His daughter was a smart girl, naturally curious about everything.

As if on cue, he sees her walking over to them.

His angel, still so young and innocent but looking like she gets bigger and bigger each times he sees her. He can’t help but feel emotional. He remembers the day she was born and he held her in his arms. The greatest day of his life.

She’s halfway towards them when she stops. She gives him the sweetest smile and calls out in a loud voice.

“Dad, I now know that you thrust your penis in mom’s -“

Jeff moves quicker than he’s ever done in his life. He covers the distance between them and grabs her before she can say anymore.

“All right honey, that’s enough. Let’s get you home.”

He hopes she doesn’t bring it up anymore. But of course he was wrong.

He has to practically beg her to stop repeating the words. And she says them in front of other people in his building. Jeff Winger, parent of the year. 

It takes all of his effort and patience to get her finish eating dinner and in bed. All the questions, some about accident babies, made him question the meaning of life. And lo and behold, just when he thought she let it go, she threw him another curveball. He was just about done tucking her into bed and ...

“Did you have other girlfriends besides mom?”

Jeff stops, still seated on the foot of her bed. He thinks for a second. He’s a lawyer so he should easily be able to get out of this. Maybe sue her for being constitutionally annoying and too curious for her own good if all else fails. 

“I had two serious girlfriends.”, he tells her.  “And other...entanglements with other women.”, he adds.

Could’ve just left it at two serious girlfriends, stupid.

His daughter stares at him incredulously. 

“What’s the boy word for slut?” she says with so much disdain it actually hurt his cold heart. 

An awkward pause, mostly for him. 

“They still haven’t made one yet.” he says, still processing what he just heard.

“It sounds like an interesting story at least. Can you tell it to me?” she asks.

“No, that’s not...it’s...no.” he lets out. 

Great. Let’s just bring up the past. Dig up all the baggage he’s been carrying all these years. 

“Just your love life before you got married. I know your childhood was rough so we don’t have to go over that.” she says thoughtfully.

Damn, was he really the parent here? Because she just sounded wiser than every adult he’s ever known. 

He considers it. A little story time couldn’t hurt. Plus free therapy for him too.

“Fine. But on one condition.” he offers.

When she just nods, he continues, “Do not ever bring up anything you learned in sex ed class again.”

She laughs. “Deal. At least in public anyway.”

”Also, I’m changing the names some facts in the story. And I’m not telling you which one’s your mom. You’ll have to put it together yourself.” Jeff decides. He’s the parent, so his rules. Artistic liberties can be taken. 

”Cool. Good.” she says casually. 

“We’ll see just how smart you are.” he challenges.

”I like it, a mystery.” she counters, not even blinking.

”All right kiddo. This is the story of how I met your mother.” Jeff begins.

”Eww, please do not start it like that. It sounds like a horrible sitcom title.” she says, disgusted.

”It’s a good show but it just doesn’t end well.” Jeff jokes.

”That’s offensive. It ends with me, dad.” she cries.

“I said what i said. But fine. Let’s just get this over with.” he says.

Here goes nothing. 


	2. Emily

**Summary for the Chapter:**

> Jeff tells his daughter about the first woman in his love life, his college sweetheart.

15 YEARS AGO

A much younger but no less confident Jeff Winger stands inside the building with lots of people cramped inside. It’s actually the school cafeteria, where they hold their all too frequent parties and dances, including this particular one. Balloons float up over their heads. The year’s most popular song is blasting away through the speakers. The place smells like if a swimming pool was filled with entirely alcohol. Which, knowing the students here, someone probably did. 

Jeff looks at the people surrounding him. Lots of familiar faces but ones he’ll most likely forget once this is all over. He keeps looking around, searching for the one he only wants to see. 

And then out of nowhere she just appears in front of him. He blinks fast twice, as if he thought his eyes were deceiving him. She’s really there. And she’s beautiful and all dressed up. She gives him a knowing smile. 

“There was this girl, let’s call her...”, current Jeff pauses, thinking of a name for his then girlfriend.

“Emily!”, his daughter says excitedly. 

“Emily. Well, I thought she was the love of my life.” Jeff continues. “We were college sweethearts. Honestly, I just wanted to get in her pants the first time I saw her.”

“Like I said, slut. But go on.” his daughter replies disapprovingly.

Back at the dance, young Jeff and Emily are now much closer to each other. 

The music’s faded, now replaced by the people counting down.

“TEN, NINE, EIGHT, SEVEN”

“You should kiss me right now.” Emily tells him.

“SIX, FIVE, FOUR, THREE”

Jeff moves in closer and their lips meet. He’s no longer aware of his surroundings. He can hear everyone faintly shouting but it’s almost as if he’s gone deaf. 

They finally break apart. They continue to stare into each other’s eyes for a few more moments. 

A few weeks later and Jeff packing his bags in his bedroom. He’s finally put the last things inside. He zips his bag close. He’s all set.

Emily sits on his bed, looking on sadly. 

“Jeff, don’t go.” she pleads.

He looks back at her, understanding her fear and disappointment. Long distance relationships almost never work out. He’s only going to be gone for a couple of months but anything can happen. 

They’re both standing now and facing one another. Jeff doesn’t say anything.

“I love you.” she lets out, trying one last time to convince him to stay.

That’s the first time she’s ever said it to him. Does she really mean it? Either way, it’s still not enough.

“I have to go, Emily. I’ll see you soon, okay?” he tells her gently.

They kiss, both not knowing if it’s for the last time. 

They now stand outside his apartment, waiting for his cab to arrive. She slips something in his hand. It’s an envelope. He stares at it questioningly looks at her.

“What’s this?” he asks.

“I need you to give that to someone. Someone I know in New York.” she says. 

“Why don’t you mail it yourself?”

Maybe that came out wrong. She looks embarassed. 

“I should’ve. And I wanted to. But I’ve put it off for too long. Their address is on there.” she confesses.

“Okay. I’ll give it to them.” he promises.

His cab arrives. They smile at each other and embrace. 

Back to the present, his daughter takes in what he just told her. She’s never seen her father open up about his past like this before. He usually hid behind his clever wit and sarcasm but this time he was being genuine and vulnerable. 

“That’s actually pretty sad. I like Emily but since she’s the girlfriend in the beginning of the story, I don’t think she’s my mother.” she states pretty confidently.

“Yeah, it was but I had never been out of Colorado in my entire life and got offered a great job opportunity which allowed me to do that.” Jeff explains. “Or so I thought.”


	3. New York, I Love You

**Summary for the Chapter:**

> Once in New York, Jeff does his best to avoid doing any work.

After getting off his plane, Jeff finally realized something. He was definitely afraid of flying. Guess that meant either very long car rides if he wanted to travel or he was going to stay here in New York for quite a while. 

He was hired as a consultant to the political campaign of one very wealthy businessman, Pierce Hawthorne. Not that he actually cared about politics. This was very much a money grab. Still, he was sure to miss having Emily around as he had no friends here. Thankfully, he could always turn on the Winger charm. 

As he arrived in their campaign offfice, he met the person he’d be reporting to. One small Asian man dressed like a Cuban cab driver. 

“So Jeff, I don’t have a lot of time right now so walk with me. I’m Chang. No questions about my race, or my height or why I’m dabbling in American politics.” he said all very fast. 

“Okay.” Jeff cooly replied.

“BECAUSE I AM A POLITICAL GENIUS!” Chang screamed while pointing at himself.

Jeff just stared. Wow. This guy was actually crazy. He was surely going to have to earn the money he’d be getting here. 

“So can you get me 500 copies of these files and a cup of coffee?” Chang asked rather sweetly this time. Sweet like poisoned honey. 

“Sure”, Jeff says. He was willing to seem like worked hard. The trick was to find someone who did actually work hard and make them do it. 

He looks around and mostly guys just drinking coffee and eating donuts. That’s where he wants to be but not people who can help him. He needs someone who looks so organized and put together. Someone who loves to please and do things for others. Or just do the work because they love it.

Finally, he sees this girl with a clipboard and a binder. Bingo.

It’s at this point in the story that Jeff’s daughter interrupts.

“Who’s that?” she asks him.

“That’s...Annie.” present day Jeff tells her. 

Back in the story, young New York Jeff heads over to Annie and taps her shoulder lightly. 

“Hey, I’m Jeff.” he says, smiling and turning on the charm all the way up to the max.

“Hi Jeff. I’m-“ she starts to say when he cuts her off.

“Yeah, sorry but I need your help. Can I ask a small favor?” he asks.

She looks a bit startled but nods. 

“Okay, what do you need?” she asks.

“I need 500 copies of these and two coffees. One black, the other I don’t really care. It’s for Chang.” he tells her.

“Oh, I know what he likes. Don’t worry, I’ve got it.” she replies happily.

About five minutes later and Jeff has barely just sat down at his small desk when Annie arrives, holding a huge stack of papers and his coffee.”

“Here you go, Jeff.” she says proudly.

Amazing. Always trust your instincts, Winger. You definitely know how to see the value in people and use them for your own personal agenda. Perfect synergy.

She doesn’t leave him yet. He sips his coffee and looks up at her expectantly.

“So, I heard you’re from Colorado.” she begins. “What made you a Hawthorne supporter?”

He almost spits out his coffee. He laughs.

“I’m not. I’m here because it’s New York and I like money.” he explains.

Her expression looks as if he had insulted her mother or something.

“Are you saying what I think you’re saying?” she asks.

“What do you think I’m saying?” he questions.

“That you’re...apathetic.” she whispers, as if it was a derogatory term.

“I’m not apathetic.” he challenges.

“Yes, you are.” she retorts.

Jeff now stands up from his chair. 

“I’m just aware. I know politics. These people have their own ambitions and care about nothing else. You think Pierce Hawthorne is going to change the world?” he tells her. 

“I do. You’re wrong. Pierce Hawthorne is a genius. He has to be. If he isn’t, then all my work here is for nothing. That’s unacceptable. He cares about women. He gets them. Read his plans, his vision. I will die protecting them. It won’t kill you to read every now and then you know.” she answers confidently, if a bit crazily.

Ugh. Well, it’s better to deal with this than actually do some work. He just yawns in reply. 

“Sorry, I just hate boring speeches. This has been great, supervisor girl.” he says with a fake smile.

“You’re the worst.” Annie just says. Maybe the weakest comeback in the history of comebacks.

Just then, someone turns up the volume on the TV in the office.

It’s on the news channel which is showing a clip of Eartha Kitt.

On the screen it reads, 

EARTHA KITT  
ALLEGED HAWTHORNE LOVER (IN AN AIRPLANE BATHROOM!)

Jeff looks back at Annie, a huge and smug smile on his face.

“Well, I guess you were right. He does get women.” he teases.


End file.
